A list of our favorite events around Annapolis, Eastern Shore and beyond for the month of June. Event dates may be subject to change.
Let’s Go! Music Festival
Let’s Go! Music Festival is back for Maryland music lovers! The festival will be June 2nd through 4th at the Anne Arundel County Fairgrounds in Crownsville and will include Chris Young, Collective Soul, Kip Moore, Priscilla Block, Larry Fleet, and many more in the lineup. The weekend will be full of games, food, and music! Get your tickets at letsgofest.com.
Annapolis Pride Parade
Pride month is here and since June 2019, Annapolis Pride has hosted a parade and festival on West Street in Annapolis. This year’s parade will be held on June 3rd to celebrate the LGBTQ+ community and embrace diversity in Annapolis. The theme will be Express Yourself: Protecting LGBTQ+ Youth and will travel from Amos Garret Boulevard to West Street, ending at Calvert Street. The festival will be held on the portion of West Street from Calvert Street to Church Circle. Find more information on annapolispride.com.
Celebrate Juneteenth
Celebrate Juneteenth in Annapolis this year! Start the weekend with the VIP Gala in African formal attire on June 16th at the Annapolis Crowne Plaza Hotel to honor the past and celebrating culturally rich history. On June 17th is the 2nd annual parade and festival! The parade will kick off at noon at the Annapolis City Docks and the festival will begin at 1:30 p.m. at the Bates Athletic Complex in Annapolis. Find all of the information and who will be up on stage at theannapolisjuneteenth.org.
Fashion for a Cause
Over a dozen local community models will come together to display new fashion from area stores on June 8th at Porsche Annapolis. Hospice for the Chesapeake is hosting the organization’s annual Fashion for a Cause, which will raise funds that will directly support its Chesapeake Kids Program. The evening will include a runway fashion show, luxury automobiles, food and cocktails from the area’s restaurants and food trucks. Find more information at hospicechesapeake.org.
Annapolis Blues Soccer
2023 is the inaugural season of the Annapolis Blues, part of the National Premier Soccer League (NPSL). And it is not too late to get your tickets. The Blues have four games this June, three of them being at their home stadium, Navy-Marine Corps Memorial Stadium. Annapolis Blues play Frederick on June 3rd at 7 p.m., Virginia Beach City on June 10th at 7 p.m., and Grove–Richmond on June 18th at 5 p.m. Get tickets and see the full schedule at annapolisblues.com.
Bands in the Sand
Get ready for a night of entertainment on June 10th at Philip Merrill Environmental Center in Annapolis. Each summer 1,600 guests gather on the beach, dance the night away, and raise a drink to Save the Bay. This party of the year is vital to the Chesapeake Bay Foundation’s mission. Find more information at cbf.org.
Asian American and Pacific Islander Festival
Join Howard County Executive Calvin Ball, the Howard County AAPI Commission, and the Inner Arbor Trust for the second annual Asian American and Pacific Islander Festival on June 11th at Merriweather Park at Symphony Woods in Columbia from noon to 5 p.m. There will be many things to do throughout the park, as well as many cultural performances on the Chrysalis stage. The vendors will also represent this dynamic community and food vendors will celebrate culture through food! Find more information at innerarbortrust.org.
Secret Garden Tour
Join the Secret Garden Tour beginning at Hammond Harwood House on June 10th and 11th from noon to 5 p.m. This tour will allow you to wander private gardens in Annapolis’ Historic District along Prince George Street, King George Street, Maryland Avenue, Hanover Street, and surrounding locations. These areas have beautiful collections of homes built in various period and architectural styles, including some of the great colonial mansions. All proceeds will benefit the 1774 Hammond-Harwood House. Find more information at hammondharwoodhouse.org.
Photo by Megan Evans Photography
Friends of The Light House 20th Annual Golf Tournament
On June 8th, the Friends of The Light House will host their 20th Annual Golf Tournament at Renditions Golf Course in Davidsonville. The Friends of The Light House provides volunteer and financial support to The Light House helping them rebuild lives with compassion by providing shelter and services to prevent homelessness and empower people as they transition toward employment, housing, and self-sufficiency. Please visit FriendsLHS.org for more information on all their 2023 events.
Capital Jazz Fest
Visit Merriweather Post Pavilion in Columbia for the three-day Capital Jazz Fest. Friday, June 2nd will kick off the festival with musicians Fantasia and Joe Thomas, while the rest of the weekend (June 3rd and June 4th) will include performances from George Benson, Ne-Yo, Incognito, The Isley Brothers, Chelsey Green, and more can’t-miss musicians! Find more information and order tickets for one, two, or all three days at merriweathermusic.com.
Every Step Counts
Bello Machre’s Every Step Counts Walk and Bike event will be held at Anne Arundel Community College on June 10th. Friends and family are welcome to come out and support people with developmental disabilities and to raise money for Bello Machre. Find more information at bellomachre.org.
National Music Festival
The National Music Festival will be in Chestertown for two weeks this June. From June 4th through 17th, the musicians will perform, with over 35 concerts ranging from solo recitals to large symphony orchestra performances with a chorus. Find more information on concerts and locations at nationalmusic.us.
Maryland Maritime Heritage Festival
The 2nd Annual Maryland Maritime Heritage Festival will be held on June 3rd in Downtown Chestertown. This nonprofit hosts the annual boat festival on the beautiful waterfront in Chestertown to showcase the legacy of traditional Chesapeake Bay Working, Sailing, Racing, and Recreational boats. Gather with others who share the love for the Bay. Find more information at mdmhf.org.
Casey Cares Rockfish Credit Sigourney Frazier
Casey Cares Rockfish Tournament
Support Casey Cares with their 6th Annual Casey Cares Rockfish Tournament based at The Bay Bridge Marina in Stevensville on June 2nd. This all-day event features fishing, fundraising, and celebrating! There will be a post-tournament Captain’s Party at the Inn at the Chesapeake Bay Beach Club. Find more information at caseycares.org.
Solstice Celebration
ShoreRivers is hosting their Summer Solstice Celebration on the banks of the Chesapeake Bay on June 24th from 6 to 10 p.m. Visit Wilmer Park in Chestertown for this signature summer event with live music and dancing along the Chester River, refreshing cocktails, delicious food, good company, and live auction. Find more information and buy tickets at shorerivers.org.
Chesapeake Bay Motoring Festival
The 7th Annual Chesapeake Bay Motoring Festival is back at Kent Island Yacht Club for two full days! One June 10th and 11th, view classic cars and boats on the majestic waterfront lawn. There will be plenty of unique antique, classic, hot rods, and sports cars surrounded by classic speed boats, yachts, and more. There will also be live music, local seafood, food trucks, libations, vendor tents, and more. Find more information at chesapeakebaymotoringfestival.org.
Chesapeake Bay Antique & Classic Boat Festival
Celebrate Father’s Day weekend with what Dad really wants: at the Chesapeake Bay Antique & Classic Boat Festival. The 35th annual festival will be held on the grounds of the Chesapeake Bay Maritime Museum in St. Michaels on June 16th through 18th. This festival will be a time for visitors to meet, share experiences, exchange information, and expand their knowledge of historic, antique, and classic boats. Find more information at chesapeakebayacbs.org.
Tour de Talbot
Tour de Fance a little too far to travel? Make it to the Eastern Shore for Tour de Talbot! On June 10th, start at the Easton Fire Hall and ride the scenic roads of Talbot County. Choose 30-, 40-, or 62.5-mile courses winding through the flat farmland and along water views, and bridges. Sign up and find more information at tourdetalbot.org.
